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Patented June 9, 1931 UNITED STATES PATENT OFFIQE LEON O. HEC'KERT, OFBRISTOII, PENNSYLVANIA, ASSIGNOIt TO COM- PANY, OF PHILADELPHIA, PENNSYLVANIA, A CORPORATION OF INSEGTICIDE Ho Drawing.

tive group, the aromatic thiocyanates being.

specificall claimed in application 367,626

mentions above.

This invention relates to insecticides, and is based upon the discovery that certain aliphatic thiocyanates, notably those ccntaining one or more negative elements or groups in the organic radical, possess the unusualinsecticidal properties characteristic of thiocyanates but are devoid of certain undesira le properties of other thiocyanates, e. g. oifensive and persistent odor and irritant properties.

.While it is recognized that the lower alkyl thiocyanates', e. g., methyl thioe anate and ethyl thiocyanate (Bull. 1313, S. Dept, A r.) possess insecticidal properties, their 0 ensive' odor, volatility and irritant action are so marked as to render them and similarly constituted compounds entirely unsuited for use as household insecticides. I have irritant action can be markedly modified or completely eliminated from the aliphatic thiocyanates by including one or more negative elements or groups such as oxygen, sulphur, iodine or other ne ative elements or groups in the organic radical attached to the thiocyanate group, Of these negative elements or groups, I have found oxygen to be of especial value, and the inclusion of an oxygen linkage, e. g. carbonyl, alkoxy or"ester group, in the organic radical is accompanied by a decided improvement in these obj actiona le properties.

I have further found that the insecticidal activity of these compounds is so great that they can be satisfactorily employed in solutions or mixtures of considerable dilution, thus allowing their employment in solutions or mixtures containing a large proportion of cheapersubstances, thereby materially refound that this ofiensive odor volatility and L Application filed May 2, 1930. Serial No, 449,864.

ducing the cost while having increased the ease of application.

, Among the compounds suitable formy in-' vention are: thiocy ano acetone, amyl thiocyanacetate, cyclohexyl thiocanacetate, secoctyl vthiocyanacetate, beta-ethoxyethyl thiocyanacetate, amyl beta-thiocyanopropionate, butyl beta-thiocyanopropionate, cyclohexyl beta-thiocyanopropionate, sec-octyl beta-thiooyanopropionate, beta-ethoxyethyl beta-thiocyanopropionate, beta-thiocyanoethyl eth l ether, beta-thiocyanoethyl hutyl ether, t o beta-thiocyano derivatives of the mono-alkyl others of diethylene-glycol, in which thealkyl group may be any aliphatic group of comparatively low molecular Weight, e. g. math 'yl, ethyl, propyl, butyl, etc. These comcontaining flies, the results obtained are' striking, it being usuall possible by this procedure to eliminatet e. flies practically completely within a very short period, c. g. five minutes, the result bein a visible accumulation of dead flies upon t e-doorl Ewample H.About 1 gram of the thiocyanate of the monobutyl ether of diethylene glycol is dissolved in sufiioient. organic solvent,-fe. g, kerosene, to make the total volume 100 cc. If this solution is used in the same manner as in Example I, the results are substantially the same. Y

Ewample' lH.-About 1 gram of sec-octyl thwcyanacetate is dissolved. in sufiicient organic solvent, e. g. kerosene, to make the total volume 100 cc. If; this solutionlfiiiffii in the same manner as in Example I,-"tlie results are substantially the same. v

Ewample lV.-About 1 gramjof'beta -ethoxyethyl beta-thiocyanopro ionate is dissolved in sufiicient or '0 so vent, e. g. kerosene,'to make the tota volume 100 00. If this solution is used in the same manner as in 5 Example I, the results are substantially the same.

What I claim is: s

1. An insecticide comprising an aliphatic thiocyanate, the organic residue of which comprises a negative group.

2. An insecticide comprising an aliphatic thiocyanate, the organic residue of which comprises a negative group dissolved in a petroleum distillate such as lierosene.

3. An insecticide comprisin an aliphatic thiocyanate, the organic resi no of which comprises an ester linkage.

4. An insecticide comprisin 1 an aliphaticthiocyanate, the organic residue of which comprises an etherhnkage.

5. An insecticide comprising the thiocyaniite pf the mono-alk'yl ether of diethylene g y 6. ,An -insecticide comprising the thiocyaniite pf the mono-butyl ether of diethylene g yco a s 7. An insecticide comprising an aliphatic mono-thiocyanate, the organlc residue of which comprises a negative grou 8. An insecticide comprising eta-ethoxyethyl thiocyanoacetate.

9. Aninsecticide comprising thiocyano ace tone. p

LEON C. HECKERT. 

